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5 Books I Should Have Read in High School

13 min

I should have read more in high school; these books could have better prepared me for college and beyond. Here are the five books I wish I had read as a teenager and why you should read them, too.

I never read as much as I should have in high school. Most of my assigned readings in class were seldom finished, and I couldn't be bothered with self-help books. After all, "I knew everything," just like any teenager.

I'm sure those of you who enjoy reading self-help books have your favorites, and I surmise that as I continue to read more in my adult life, this list has the potential to change considerably. But for now, here are my recommendations for five books I think every young man should read before he officially enters adulthood.


It's a timeless classic. Take nearly any modern self-help book you know of, and there is a good chance that this beautiful offering from Dale Carnegie partially influenced it.

Initially published in 1936, this book receives periodic updates; however, the fundamental lessons remain unchanged. Carnegie has a simple but effective way of writing that gets right to the point. You get a sense that this book was written for everyone.

This book is about winning people to our way of thinking, not by arguing or belittling them, but by appealing to their interests. Furthermore, it attempts to help us empathize more effectively with others. Almost a century after the book's publishing, people still fail to relate to others. This book enables us to handle people in virtually any type of situation.

In my opinion, this text is quintessential for any young person looking to blaze their trail in life, a path that will undoubtedly converge with the courses of others seeking to achieve their hopes and dreams. Much of our relational problems and other disputes are predicated on our lack of understanding and general disinterest.

Two fundamental behaviors organize Carnegie's book:

Fundamental Behavior #1: Take a Genuine Interest in Others

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” - Dale Carnegie

Nobody cares as much about what YOU want as they care about what THEY want. If you are trying to gain influence over others and win them to your way of thinking, you have to start by taking a genuine interest in whatever they are passionate about.

In other words, what interests them ought to fascinate you. True leaders who are worth their salt will recognize that to succeed, they must have a vested interest in the achievements of those who follow them because their followers' successes will culminate in the organization's success and, by extension, their success.

There is a big difference between commanding respect and demanding it.

Can you guess which method someone in a position of authority can better garner more respect and admiration?

On average, people will never go the extra mile for those in charge unless they feel their leadership is vested in their happiness and well-being. This is the bedrock for trust, and Carnegie knew that fact well.

"People do not care about how much you know until they know how much you care." - Theodore Roosevelt

Fundamental Behavior #2: Give Frequent Praise

When people pay us genuine and honest compliments for our work, our admiration for them increases. The keywords here are genuine and honest. If these hold and no ulterior motivations are present, you can bet that the person receiving the praise will feel more inclined to engage and entertain the one issuing that praise.

After all, it feels good to be recognized for our efforts; words of affirmation uplift everyone.

"Begin with praise and honest appreciation. Call attention to people's mistakes indirectly. Talk about your own mistakes before criticizing the other person. Ask questions instead of giving direct orders. Make the fault easy to correct. Make the other person happy about doing what you suggest." - Dale Carnegie

I have witnessed it in the military and throughout other landscapes of life. There are people in positions of influence who choose to ignore the feelings and thoughts of others. In certain situations, it may be necessary; however, as a rule, it should be known that no soundly-minded individual wants to have their thoughts and feelings ignored.

So then, why do people who are tasked with leading others choose, in some instances, to ignore praise for good work?

Because it is difficult to sustain interest in other people's thoughts and feelings, if it were easy, everyone would do it...

If you are either in a position of influence or seeking to influence others in a meaningful capacity, you would do well to understand what Carnegie teaches in his book.

"I can look back at my own life and see where a few words of praise have sharply changed my entire future. Can't you say the same thing about your life?" - Dale Carnegie


Here is a book I recommend to everyone I meet, quite literally. Another simple but effective offering, Gary Chapman's equally profound The Five Love Languages, is a timeless, easy, and elegant guide to understanding how people give and receive love. Even if we are not in a place where we wish to pursue romantic relationships, I still cannot recommend this book enough.

This book has helped me better understand friends, family, and even people I have worked with in stressful environments because it has helped me know how best to communicate with them and meet their needs. When my wife and I were dating, we read this book together in preparation for the journey ahead of us, and even though we had read it at least once before meeting one another, we still managed to find new meaning and appreciation after reading it an additional time. Trust me when I tell you it is worth reading and re-reading.

As humans, we all share the desire to feel loved, needed, and appreciated. By using this simple yet practical guide to understand others and ourselves, we can enhance virtually all our relationships in life for the better.

For our romantic relationships, we need to recognize how best to give love to our spouse and understand how we receive it for ourselves. As Chapman puts it, this feeds into keeping our respective "love tanks" full.

“Real love is a kind of love that is emotional but not obsessional. It is a love that unites reason and emotion. It involves an act of the will and requires discipline, and it recognizes the need for personal growth.” - Gary Chapman

The Five Love Languages described in Dr. Chapman's book are as follows:

I. Words of Affirmation - using our words to make people feel appreciated by complimenting or acknowledging their efforts. For people, simply verbalizing our appreciation can make or break their day.

II. Quality Time - using time spent together to help your partner feel loved. This refers to time engaged with one another, not by watching television or simply remaining present, but by genuine engagement.

III. Acts of Service - doing the things your partner wants you to do and showcasing love through your services.

IV. Receiving Gifts - described as the physical "proof" of your love, this can help your partner feel loved because it shows that when you procured an item, you were thinking of them.

V. Physical Touch - not limited to sexual acts, this language refers to the more nuanced deeds, such as rubbing your partner's back or placing your hand on her/his shoulder. Kiss them before you leave, or a physical embrace when you are reunited. On some level, most people enjoy these physical acts, but for those who have this primary love language, it is all the more essential to them.

“People tend to criticize their spouse most loudly in the area where they themselves have the deepest emotional need.” - Gary Chapman

At first glance, to those who have not yet read the book, you may begin to instantly identify one or two love languages that you believe to be yours. However, if you read it from cover to cover (which isn't difficult to do given the book's relatively short length), you will be surprised at how much your preconceptions will change by the end of the reading.

Dr. Chapman gives examples via personal stories that help the reader see how these languages may be translated, and the genius resides in their simplicity. I never had more "aha!" moments than I did when reading this book (perhaps aside from Dale Carnegie's How to Win Friends & Influence People). This is a great starting point for anyone looking to get married one day or work professionally in an environment of people with varying backgrounds and beliefs.

BOOK #3: RICH DAD POOR DAD by Robert Kiyosaki

Much to my dismay, schools fail to teach young people financial literacy... I know that this statement alone is enough to stir up quite a bit of controversy, but love it or hate it, building wealth in life is not nearly as much about following the "deferred-life path" as understanding how money works.

In his book Rich Dad Poor Dad, Robert Kiyosaki makes it very clear that there are effectively two types of people in this world:

  1. Employees (those who work for money)
  2. Entrepreneurs (those who make money work for them)
“Financial struggle is often the result of people working all their lives for someone else.” - Robert Kiyosaki

I am not here to convince you that employees are better or worse than entrepreneurs, nor is Kiyosaki; in fact, he talks about the importance of both. However, the "deferred-life path" suggests that the best way to navigate life is to go to a good school, work hard, make good grades, compete to earn a job with solid pay and excellent benefits, and work toward retirement.

Kiyosaki unabashedly proclaims that these people are ultimately misguided if they hope to build wealth in the short term. I certainly won't claim that I agree; however, I can tell you that abiding by life's "deferred path" does not always equate to building sustainable wealth, so keep an open mind and be willing to draw into question what you think you know.

“Often in the real world, it’s not the smart who get ahead, but the bold.” - Robert Kiyosaki

Kiyosaki decides to first focus on the mindset of the wealthy and encourages the reader to become more financially savvy in accounting, investing, and law. Kiyosaki argues that these are fundamental because by learning to speak these dialects better, anyone can learn the "language" of money.

What inspired me the most when I first read this book was how Kiyosaki describes a life where we can all control our destinies and obtain financial security. Some great key points that he makes are as follows:

“Success is a poor teacher. We learn the most about ourselves when we fail, so don’t be afraid of failing. Failing is part of the process of success. You cannot have success without failure.” - Robert Kiyosaki


Not everyone is born or meant to be a leader, and if we're being honest, not everyone should be or desire to be one... That is quite alright, but if you're not a leader, then you're a follower, and any faithful follower ought to have expectations of their leaders just as leaders ought to have standards and expectations for themselves.

Leadership guru John C. Maxwell has written countless books on leadership. I could recommend any number of them as a part of this list. As a starting point, I loved every bit of Maxwell's The Five Levels of Leadership for the same reasons as all the aforementioned books: it's simple, straightforward, and complete.

Leadership is something that I have been passionate about since I was in high school. I joined the Navy, attended a military college, and was commissioned as an officer because I wanted to lead others and inspire them to achieve more for themselves. Because of those same passions, I started Gentleman's Flair.

In my continual leadership journey, I have stumbled, become humbled, flat-out failed, and learned much about what earning the title of a leader means. Much of that journey began with this book. Maxwell's five levels are:

I. Position - where everyone must start, but the position does not make the leader.

II. Permission - people choose to follow you because they want to.

III. Production - understanding how to motivate and inspire people to produce results and get things done.

IV. People Development - learning how to produce other leaders.

V. Pinnacle - your reputation becomes known because you have demonstrated mastery of the aforementioned levels and are in the leadership game for the long haul.

I have worked for some great leaders and some awful ones. I hope to continue growing as a leader and reach the pinnacle of leadership someday. Until then, I take it day by day.

I appreciate Maxwell's levels because they depict a process where every level feeds directly into the next. He clarifies that you can ascend the "ladder" of leadership to the next one only after mastering each single level.

During my time in the military, people often took their professional positions (and themselves) too seriously. Yes, roles within bureaucratic and hierarchal systems are essential for order. Still, good leaders recognize that it is always more effective and rewarding to lead people who actively choose to be led by you, not because they have to, but because they want to. "Because I said so" is a poor demand and reasoning for anything.

"Positional leaders focus on control instead of contribution." - John C. Maxwell

Maxwell teaches that the point of climbing the leadership ladder is to generate new leaders. He speaks often of the necessity to add value to others, and I agree wholeheartedly because this benefits our society. Getting to Levels 4 and 5 in our leadership journey is seldom easy. Some people want to fast-track their leadership trajectory but fail to recognize that leadership success isn't something they alone can dictate.

"It's not the position that makes the leader; it's the leader that makes the position." - John C. Maxwell

BOOK #5: YOU ARE GOOD ENOUGH by Robert J. Furey

This one is simple to grasp and a relatively quick read, much like the previous books. What makes this book unique (to me) is that it vividly introduces the concept of shame.

This book is for people who deal with feelings of inadequacy, specifically those whose sense of inadequacy has become such an opposing force in their lives that it prevents them from moving forward.

On some level, we have all felt that we were not good enough; for some of us, we become paralyzed by the thought of ridicule and failure. No one is exempt from these feelings, and even those who become wildly successful face these burdens (in some cases, more than the average person).

Referred to by the author as a "hidden epidemic," shame is ultimately defined as "a feeling of self-loathing brought about by thoughts of inadequacy." When we are ashamed, we feel a great distance between the person we perceive ourselves as and the person we wish we were. Much of this ultimately leads to a desire to conceal ourselves because we hate who we are.

"Guilt is the feeling that 'I've done something wrong.' Shame, on the other hand, laments the fact that 'I am something wrong.' Shame runs deeper than guilt; it gets rooted much further into our beings." - Robert J. Furey

This is a severe issue because attempting to conceal ourselves makes intimacy very difficult, if not impossible. Furey then describes how shame can afflict us in three distinct forms:

1. Mild Shame: Often exemplified in people who are competitive but notoriously tough on themselves, drawing comparisons between themselves and others. These comparisons cause augmentation for one's perception of their flaws when they feel they do not measure up, eventually instigating a need to hide those flaws.

2. Moderate Shame: Occurs when mild shame is extended, and the resulting pain is more significant than mild shame. Although those who suffer from moderate shame possess a feeling of general hope, it is more the thought that things could be worse amidst a flood of emotions that can cause those afflicted to feel stuck in their pain more than those who suffer from mild shame.

3. Severe Shame: The negative thoughts and feelings become unbearable, and a person's everyday life becomes almost impossible to navigate. Finding hope can feel very much outside the realm of possibility for those afflicted by severe shame.

"As you become more accepting of yourself, you will become more like the person you really are. Life will reach out to you and invite you to live and learn. The referees will fade from your world. At one time, it seemed as if everyone was judging you, but no more. And all those who you thought were superior to you, well, their imperfections become more apparent. People will become more real to you. Gradually, the world will become friendlier, and in time, fear will be replaced with gratitude." - Robert J. Furey


What are you doing if you aren't finding ways to improve yourself each day? It took me too long to pick up and read these books (or books like them) and finish them cover to cover.

The most important asset that anyone can invest in is their mind. Knowledge is power, and learning to navigate a world with relationships to cultivate, organizations to influence, and assets to acquire is paramount to living a successful and purposeful life. I encourage you to read any of these books if you haven't already.

As much as they have expanded my mind, they have also shaped my heart.

How to Win Friends & Influence People by Dale Carnegie

The Five Love Languages by Gary Chapman

Rich Dad Poor Dad by Robert Kiyosaki

The Five Levels of Leadership by John C. Maxwell

You Are Good Enough by Robert J. Furey



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